I effectively restarted last night. But I'm going to attach my save anyway. Thanks for being willing to take a look at it for me.
Hmm, it seems the Max icon has vanished as well. I'm not sure which of these is the most applicable, so I'm attaching the whole lot of them.
It's not actually that big of a problem, I just bought Ashley some lingerie after overhearing her argument with Claire. This I could redo in about 30 minutes.
Oh, no problem. Ok, in the first save, "Glodbog (24 - 10.00)", you'll need to buy more wine from the supermarket and offer Claire a glass at 21:00 before you give her a foot rub in the living room, then help her to her bedroom. Once that scene ends in her room (and her stats increase), her hints will show back up.
In that same save, now that you have the babydoll lingerie for Ashley, go to her room at 15:00 (make sure it's on a weekday) and give her the new outfit.
Now, in your other save, "Glodbog (2 - 08.00)", I didn't see any problems there. Claire's hints are showing.